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Day 20 - Part 2 - Breaking the Tiny Caged Cock

Happy New Year - Inverted Cage for Sissy!

Day 8 - Just the Tip (part 3/5)

Day 31 Part 1 - Last Day of Teasing

Day 16 - More Ass Training

Dirty Talking Wife Part 3

Locktober Day 24 - Part 3/4 - Break those Balls

Day 15 - Goodnight Squeezes

Locktober Day 18 Tease - Part 2

Day 23 - Breaking Sissy Part 2

Dirty Talking Wife Part 1

BBC on a Saturday Morning (3/4)

Day 23 - Breaking Sissy Part 1

Day 31 Part 3 - Last Day of Teasing

Day 8 - Working it in! (part 4/5)

Do I punch like a girl?

Day 17 (Part 1) Smacked Balls

Dirty Talking Wife Part 5

Day 20 - Part 1 - Crushing & Kicking

Stomped his balls to a pulp, and broke his shaft again with inverted steel cylinder chastity!

Day 8 - Get on the Floor! (part 2/5)

Dirty Talking Wife Part 2

Day 31 Part 2 - Last Day of Teasing

Dirty Talking Wife Part 4